The Freelancer’s Secret to Learning Any New Skill

As a designer, developer and all around creative person, there are some skills that likely came very naturally to you. The learning experience just sucked you in and you enjoyed yourself enough that you picked up this new talent in an impressively brief timespan.

Other skills however, prove to be more difficult. Sometimes you can feel like your brain is simply full and that there’s no more room for this old dog to learn a new trick. How do you overcome this mental block and force yourself to learn that new skill you’ve been wanting to pick up? There’s a secret that many freelancers know well that is a sure fire way to learn almost anything new in your given field. Read on to see what it is!

The Problem

Let’s say you’re a great designer and have some impressive HTML/CSS chops, but can’t write a line of JavaScript to save your life. “No problem” you think, “I learned all of that other stuff, I can do this!”

So you fire up Lynda.com, start watching some video tutorials, and then remember that you should definitely tweet about how great Lynda is for learning new stuff, which leads to a solid hour of messing around on Twitter because, let’s face it, those videos had you bored out of your mind.

No matter, what you really need is a book. A good old paper and ink lesson doesn’t have all the distractions of your computer. So you head to Amazon, buy the best manual you can find, then take a break for a few days while you wait for it to arrive. When it does arrive, you block out a few hours, find a nice comfy chair in a quiet spot, crack open the book, then awake an hour later to find your face cemented to the pages with drool.

What’s the matter with you? Have you suddenly become educationally incompetent? Why was learning so easy at the start of your career and so difficult now? Should you keep searching for alternative learning techniques or does the problem lie elsewhere?

But I’m Normally So Productive!

For me, and I’m sure a ton of others, the problem in situations like these turned out not to be so much the method of education as the circumstances surrounding the education.

I’m a workaholic who juggles at least three jobs at any given time, often several more. At work, I strive on stress and leverage my psychological need to meet deadlines at all costs to stay productive. If we remove that stress from the equation, I’m not really the same person.

When I’m casually attempting to learn something in my free time, I don’t feel pressured to produce. Consequently, I’m prone to distraction, procrastination, and all other manner of avoidance that leads to my ultimate frustration at my inability to pick up a new skill. This effect is exponentially worsened by all of that work-related stress, which leads me to drop the education attempt in favor of simply using my free time to work more.

Necessity Is The Mother of Education

I recently had a revelation regarding my ideal environment for learning. It all started with a job offer. Someone approached me and asked me to take on a huge project that involved producing over a dozen professional quality videos.

Let’s be clear, I’m a designer and a photographer, but I’m definitely not a video guy. I’ve always been fascinated by the lure of video, but have never really had the time to jump in and master the art. In fact, I had never really done any video work at all, even on a personal, home movie level. I know there’s a “record” button on my beloved 5D Mark II, but I had never used it.

The time requirements for this project were beyond what I could really commit to, the deadline was sooner than I wanted it to be and the requisite skills were way out of my ballpark. I literally had no idea how I would deliver what they were asking me to produce. My answer: “Sure! I’d love to!”

The Missing Ingredient

Right away I found that I was in over my head. I quickly realized that I needed more equipment than a camera (microphones, backdrops, lights, etc.), and that getting the setup that I wanted would be costly, time consuming and frustrating. I also realized that I didn’t possess the software necessary for such a feat, nor did I have any experience with any video editing software. In short, I was screwed. My stress indicators lit up like a Christmas tree.

And there it was. My secret serum for education was finally present. Faced with the fact that I had promised to deliver a product, I realized that I had given myself no out, no room for slacking off or getting distracted. The situation I had created was strictly sink or swim. I was staking my reputation with some important people on this project so I took the only available course of action that I could see: I worked my butt off.

I did a ton of research, decided on some equipment, created a project outline, filmed what I needed to film and spent ages on an outdated Mac that’s horrible for video, chopping it all up and piecing it together in between spinning beach balls and progress bars. Eventually, I had my first video. The process was brutal, but I had done it. The fruits of my labor were clear as day. That little victory was so incredibly encouraging that I pressed on. Video two was even easier! After that, I really hit my stride and things became much smoother.

The Secret To Learning Anything

The moral of this story is clear: if I want to learn something, the best way for me to do it is to get a job doing it. Looking back over my career, I could suddenly see that literally all of my notable skills had evolved along similar lines.

I landed an amazing print design gig at the age of 18, despite the fact that I didn’t know how design worked in the least. I had to learn, and quick, so I did. Similarly, I wasn’t able to make the jump to web design and coding until I landed a job that required me to pick it up. Photography was the same, I knew how to take a picture but didn’t really understand my camera on a deep level or learn about professional post-processing workflows until a friend asked me to help him shoot a few weddings.

I would wager that I’m not the only one who tends to learn under duress better than in a casual, no-stress environment. Even formal education applies these constructs through homework with tight deadlines and difficult testing procedures. In college I pulled a 4.0 not because I was particularly smart, but because I felt pressured to do get my work done to the best of my ability.

Find a Gig That Challenges You

My message here is simple: if you want to learn something new, find someone who will pay you to do it and commit to a deadline. Nothing will push you to greatness quite like the fear of failure and embarassment.

It’s probably one of the more intense methods of self-forced learning that you can find, but you’ll find that once you pull it off, you’ll have an immense amount of pride in what you were able to produce, not to mention an awesome new bullet point for the skills section of your resume!

Results May Very

I fully realize that it’s not possible to paint every creative on the planet with such a broad stroke. There are no doubt plenty of people out there who fold up like origami under stress and are more prone to miss the deadline and/or drop the project than complete it.

Though I question your choice of profession if this describes you, I do think you can be helped by my story as well. Focus on the part where I examined the situations from my past where I was able to pick up a new skill and looked for a common thread. Perform this analysis on your own skill set. The circumstances that successfully worked for you in the past will likely work again, you just have to manufacture a similar situation. Your goal is merely to find your particular learning style and exploit it. Mine is a crazy kamikaze death dive where I pull out at the last second and somehow walk away unscathed and better for the experience, yours might be something much more relaxed and stress-free. Though I do recommend that you give my way a shot at least once, because it really is quite effective.

How Do You Learn Best?

There you have it, I have single handedly broken down the wall standing between you and expanding your collection of professional skills. You’re welcome.

On a serious note, I’d love to hear what you think about all this. Do you find that the best way to learn a new skill is to take on a job that requires it? Why or why not?